Seaside stay .Your stay at this Key West Historic District vacation home places you within 2 miles (3 km) of Duval Street and Florida Keys Beaches. Southernmost Point and Mallory Square are also within 2 miles (3 km).
Ernest Hemingway Home and Museum - 18 min walk - 1.0 mile
South Beach - 18 min walk - 1.0 mile
Southernmost Point - 20 min walk - 1.1 miles
Getting around
Key West Intl. Airport (EYW) - 7 min drive
Restaurants
Circle K
Dions Truman & White - 3 min walk
Sandy's Café
Moose Lodge - 6 min walk
Rainbow Cafe (MARC) - 8 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!
CATCH YOUR SECOND WIND… Unplug in this newly renovated and elegant refuge, a place of tranquility with an island ambiance. Equipped with 2 bedrooms and 2 bathrooms, this home welcomes you into a peaceful setting within the desirable district of The Meadows. ***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGE
DETAILS & AMENITIES… Welcome in to an inviting, open floor plan boasting vaulted ceilings, hardwood floors and stunning wooden beams ready to entertain your crew for your getaway to Paradise. A fully equipped kitchen allows for seamless meal prep to enjoy together at the dining table for 6. Enjoy the bright and cheery living space with cozy furnishings and a TV for your lazy days in with gorgeous views beyond pocket doors of your outdoor oasis. This home is equipped with Youtube TV for live steaming.
SLEEPING ARRANGEMENTS… Sleep tight in one of two cozy bedrooms both equipped with storage space and flat screen TVs. The primary king suite comes with an en suite bathroom with a double sink vanity and jet tub/shower combination. The second bedroom has a Queen Murphy bed and desk so the room can also be used as an office space. The second bathroom lies in the hallway with a shower/tub combination.
OUTDOOR LIVING… Soak up your surroundings as you head out to your private backyard dream tucked within lush and vibrant foliage. Cool off in the pool which comes heated in the winter month and dine al fresco in the island breeze equipped with a gas grill. Lounge on your private front porch over your morning cup of coffee as you dream of your days adventures ahead. The Meadows district is a charming and convenient location to downtown Key West, yet tucked away for a peaceful evenings rest.
PARKING... There is one parking space making coming and going a breeze.
PETS... Dogs are considered at this home and a pet fee is required. Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests.
MULTI MONTH RESERVATIONS... For monthly reservations, the following fees will be added PER MONTH: Mid-stay clean Pool/hot tub heating fee (if applicable) Pet fee (if applicable)
BOOKING DATES... This home is only available as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception.
CONCIERGE SERVICES... Enjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!
CANCELLATION... Bookings canceled at least 90 days before the start of stay will receive a 100% refund.
Cancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s).
YOUR SLICE OF PARADISE AWAITS…
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Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
Key West Historic District
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
Deadbolt lock
General
Unit size: 1,142 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets are welcome
Service animals are exempt from fees
Children and extra beds
Children are welcome.
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.
Property Registration Number 25230-138749
Property is also known as
2450-214090
Frequently asked questions
How close is SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! to the airport?
This vacation home is 2.9 mi (7-min drive) away from the Key West Intl. Airport (EYW) airport, the closest popular airport to the property.
Does SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! have an airport shuttle?
Airport shuttle services are not available at this vacation home.
How close is SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! to the beach?
This vacation home is 0.9 mi (3-min drive) from Florida Keys Beaches and 1.1 mi (6-min drive) from South Beach. Don't forget your sunscreen!
Does SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! offer free breakfast?
This vacation home does not offer free breakfast.
Is there a casino at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?
No, there is no casino at this vacation home.
What time is check-in at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?
Check-in begins at 4:00 PM.
Is there free parking at SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool!?
Free parking is not available at this vacation home.
Does SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! have a pool?
Yes, there's a private pool.
Does SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! have a spa?
There are no spa services available at this vacation home.
How close is SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! to downtown Key West?
This vacation home is 0.8 mi away from Key West.
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/ Pool! Reviews
Reviews
9.8
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 8 out of 9 reviews
10 - Excellent
8
Rating 8 - Good. 1 out of 9 reviews
8 - Good
1
Rating 6 - Okay. 0 out of 9 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 9 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 9 reviews
2 - Terrible
0
6.0/10
Cleanliness
Reviews
From a partner site
10/10 Excellent
A guest from Montreal, Quebec
Feb 17, 2023
Best vacation!
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Brian was helpfull I loved my stay and I even rebooked for next year
A guest from Montreal, Quebec
From a partner site
10/10 Excellent
Anonymous
May 8, 2025
Great experience
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
I spent two months at this property and loved it. It is a peaceful neighborhood, and the property is beautiful—just as advertised in the pictures. I recommend it highly. Also, the property manager and management company are first rate and very responsive.
Anonymous
From a partner site
10/10 Excellent
John R.
Sep 2, 2024
Perfect house for the summer
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We rented this house for 3 months, and was close enough to all the action, and also super convenient for parking and access to the park to walk our dogs twice a day. We loved it. Not to mention a pool to cool down in!
John R.
From a partner site
10/10 Excellent
Melissa S.
Jun 25, 2022
Wonderful trip
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Second Wind property was a wonderful respite from the cold climes of Wyoming. The location and proximity was perfect for us. The neighborhood was quiet, neighbors lovely, house was comfortable. Team Truman and Company are excellent!
Melissa S.
From a partner site
10/10 Excellent
Page W.
Apr 5, 2023
March 2023 Second Wind Stay
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Beautiful cottage in great location in Key West. Rental team superb throughout, property manager Brian was great and immediately responded to any issues or concerns. Highly recommend.
Page W.
From a partner site
10/10 Excellent
Alicia W.
Jul 7, 2022
Wonderful Retreat
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
Everything was exactly as we hoped it would be. Good location with off street parking (a definite plus). The one problem that we had (lock problem) was quickly and efficiently solved by Brian. Definitely would recommend to friends 🤙.
Alicia W.
From a partner site
10/10 Excellent
Dwight U.
Mar 20, 2023
Second Stay at Second Wind.
Rating Details:
The property manager was very helpful.
The vacation rental was very clean.
I was very happy with the location.
I was very satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
This was our second stay at this deluxe house on Albury Street. The perfect home in Key West. We brought our bikes and never drove our car again for the month. You are an easy bike ride from Duval Street and all it has to offer. Once you are home in this private little oasis the fun really begins. The back yard and pool are very secluded and very beautiful. A tropical heaven!
Dwight U.
From a partner site
10/10 Excellent
John M.
Dec 23, 2023
A pleasant stay at Second Wind
Rating Details:
The property manager was very helpful.
The vacation rental was spotless.
I was very happy with the location.
I was more than satisfied with the condition of the vacation rental.
Overall, I recommend this vacation rental.
Reviewer Comments:
We're having a terrific time. We've been here for 7 weeks with 10 days to go. The location is perfect for us, in a quiet neighbourhood (the Meadows) but an easy walk or bike ride to anything we want to do. The house itself is bright and airy. The housekeeping and pool/landscaping services are excellent. The property management team has been very helpful and are quick to respond. If we could make some minor suggestions, they would be: to add towel racks to the principal bathrooms and more dishware, especially saucers for the cups, in the kitchen (which is very well-appointed otherwise). The addition of a light over the dining room table would be helpful. We find the living room sofa a bit too deep to be comfortable for TV viewing. These are relatively minor issues and we've loved our stay here.
John M.
Verified
8/10 Good
Timothy D.
Dec 11, 2021
Liked: Check-in, location, listing accuracy
Misses
No garbage disposal or ice maker. The freezer would stay open after you shut the fridge.
The landscapers came once during our stay and they were there on the day we left. The yard and street were a mess.
The lack of curtains in the living room provided NO privacy. It was like we were in a fish bowl.
The light over the stove did not work.
The front gate is falling apart.